4604-28-8

Upstream product

• 68089-86-1 chloromethyl(triphenyl)phosphonium iodide 
• 100-52-7 benzaldehyde 
• 67-56-1 methanol 
• 64-17-5 ethanol 
• 88211-07-8 Benzylchlorocarbene 
• 88211-05-6 3-benzyl-3-chloro-3H-diazirine 
• 4110-77-4 (E)-β-chlorostyrene 
• 64-19-7 acetic acid 
• 3883-13-4 2,2,2-trichloroethylbenzene 
• 2000-43-3 2,2,2-trichloro-1-phenylethanol 
• 621-82-9 Cinnamic acid 
• 57918-63-5 (Z)-styryl iodide 
• 3220-49-3 phenyl copper 
• 156-59-2 cis-1,2-Dichloroethylene 

Downstream Products

• 18684-72-5 α-Chlor-trans-styryllithium 
• 71129-92-5 chloro-2 dimethylamino-1 phenyl-1 ethylene 
• 140-10-3 (E)-3-phenylacrylic acid 
• 40132-69-2 (Z )-1-(2-cyclohexyl-1-ethenyl)benzene 
• 85429-45-4 C₁₄H₂₀⁽²⁾HN 
• 71129-94-7 C₁₄H₂₀LiN 
• 85429-46-5 Dimethyl-((E)-2,3,3-trimethyl-1-phenyl-but-1-enyl)-amine 
• 33119-75-4 2-Brom-3,3-dimethyl-1-phenyl-1-butanon 
• 57847-43-5 (+/-)-2,3,3-trimethyl-1-phenylbutan-1-one 
• 886-65-7 trans,trans-1,4-Diphenyl-1,3-butadiene 
• 5808-05-9 (1Z,3E)-1,4-diphenylbuta-1,3-diene 
• 5807-76-1 (1Z,3Z)-1,4-diphenylbuta-1,3-diene 
• 84710-16-7 (Z)-β-chlorostyrene cation 
• 84710-15-6 (E)-β-chlorostyrene cation 

Relevant academic research and scientific papers

Shelf-Stable (E)- A nd (Z)-Vinyl-λ3-chlorane: A Stereospecific Hyper-vinylating Agent

We report the first stereoselective synthesis of stable (E)- A nd (Z)-β-chlorovinyl-λ3-chlorane via direct mesitylation of 1,2-dichloroethylene with mesityldiazonium tetrakis(pentafluorophenyl)borate under mild reaction conditions. The structure of the (E)-vinyl-λ3-chlorane was established by single-crystal X-ray analysis. Because of the enormously high leaving group ability of the aryl-λ3-chloranyl group, vinyl-λ3-chloranes undergo not only SNVσ-type reaction with extremely weak nucleophiles such as perfluoroalkanesulfonate, iodobenzene, and aromatic hydrocarbons but also coupling with phenylcopper(I) species.

Continuous Flow Chlorination of Alkenyl Iodides Promoted by Copper Tubing

A simple continuous flow synthesis of alkenyl chlorides from the corresponding readily available alkenyl iodides in copper reactor tubing is described. A variety of alkenyl chlorides were obtained in good to excellent yields with full retention of the dou

Iron-Catalyzed Cross-Coupling of Alkynyl and Styrenyl Chlorides with Alkyl Grignard Reagents in Batch and Flow

Transition-metal-catalyzed cross-coupling chemistry can be regarded as one of the most powerful protocols to construct carbon–carbon bonds. While the field is still dominated by palladium catalysis, there is an increasing interest to develop protocols that utilize cheaper and more sustainable metal sources. Herein, we report a selective, practical, and fast iron-based cross-coupling reaction that enables the formation of Csp?Csp3 and Csp2?Csp3 bonds. In a telescoped flow process, the reaction can be combined with the Grignard reagent synthesis. Moreover, flow allows the use of a supporting ligand to be avoided without eroding the reaction selectivity.

Reaction of Styrene with Chlorine Dioxide

Reaction of styrene with chlorine dioxide under various conditions selectively produces 1-phenyl- 2-chloroethanone, with 1-phenyl-2-chloroethanol, 2-hydroxy-1-phenylethanone, (1,2-dichloroethyl)benzene, (2-chloro-1-phenyl)ethene, and (1,2,2-trichloroethyl

A General Copper-Catalyzed Vinylic Halogen Exchange Reaction

An efficient and general system for the halogen exchange reaction in alkenyl halides has been developed. Upon reaction with catalytic amounts of copper iodide and trans-N,N′-dimethylcyclohexane-1,2-diamine in the presence of tetramethylammonium chloride or bromide, a wide range of easily accessible alkenyl iodides can be smoothly transformed to their far less available chlorinated and brominated derivatives in excellent yields and with full retention of the double bond geometry. This reaction also enables the chlorination of bromoalkenes and could be extended to the use of gem-dibromoalkenes.

Development of a general copper-catalyzed vinylic Finkelstein reaction—application to the synthesis of the C1–C9 fragment of laingolide B

An efficient and broadly applicable procedure for the copper-catalyzed vinylic Finkelstein reaction is reported. Using a simple, readily available and cheap catalytic system, a broad range of alkenyl iodides and bromides can be smoothly converted to their lower homologues with high yields and full retention of the double bond geometry. Key features of this vinylic Finkelstein reaction are its broad applicability, enabling the conversion of readily available alkenyl iodides to their less available brominated and chlorinated counterparts, and the mild reaction conditions compatible with a range of highly functionalized substrates. The potential of this vinylic halogen exchange reaction in total synthesis and medicinal chemistry was demonstrated by its successful use for the synthesis of the C1–C9 fragment of laingolide B and for the late-stage modification of drug-like molecules. The extension of this halogen exchange to the acetylenic and allenic Finkelstein reactions is also reported.

Solid-phase oxidative halodecarboxylation of β-arylacrylic acids with the ceric ammonium nitrate-alkali halide system

The solid-phase oxidation of cinnamic, 4-methoxy- and 3,4-dimethoxycinnamic acids with Ce(NH4)2(NO3)6-MHal system leads to β-halostyrenes. Similar procedure in the absence of a metal halide results in a cleavage of the C=C bond giving the corresponding benzaldehydes.

A mechanistic study of the chromium(II)-mediated transformations of trichloromethyl alkyls and carbinols: evidence for carbene, carbyne, and carbenoid intermediates

Using CrCl2 in THF at room temperature, trichloromethyl carbinols and trichloromethylalkanes are readily transformed to the highly reactive α-chlorocarbenes, carbynes and α-chloro-α-chromium(III) vinylidene carbenoids. A mechanistic study is carried out to determine the nature of the intermediates.

Determination of the photolytic decomposition pathways of benzylchlorodiazirine by C60 probe technique

By employing C60 as a chemical probe, the photolysis of benzylchlorodiazirine has been proposed to form carbene and the rearranged products via the excited state.

Preparation of (Z)-1-halo-1-alkenes and (Z)-1-halo-2-alkoxy-1-alkenes using Cr(II/III) and Fe(0)

Reduction of 1,1,1-trihaloalkanes by Cr(II) or Cr(III) regenerated by Fe(0) in moist tetrahydrofuran at room temperature stereoselectively generates (Z)-1-halo-1-alkenes and (Z)-1-halo-2-alkoxy-1-alkenes in good to excellent yields. Georg Thieme Verlag Stuttgart.